7-(8-azabicyclo[3.2.1]oct-2-en-3-yl)-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one → 7-(8-azabicyclo[3.2.1]oct-3-yl)-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one

HRID 394183노트

반응식

HRID 394183 반응식
[CH:1]12[NH:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][C:3]([C:9]1[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][C:15](=[O:27])[N:16]3[C:19]3[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:26])=[C:11]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=3[Cl:35])[N:10]=1)=[CH:2]2>C(OCC)(=O)C.O=[Pt]=O>[CH:5]12[NH:8][CH:1]([CH2:7][CH2:6]1)[CH2:2][CH:3]([C:9]1[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][C:15](=[O:27])[N:16]3[C:19]3[C:20]([Cl:26])=[CH:21][CH:22]=[CH:23][C:24]=3[Cl:25])=[C:11]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=3[Cl:35])[N:10]=1)[CH2:4]2

참가 물질

4

반응물 1

HCID 226479477-(8-azabicyclo[3.2.1]oct-2-en-3-yl)-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one

생성물 1

HCID 226481247-(8-azabicyclo[3.2.1]oct-3-yl)-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one

시약·촉매·용매 2

HCID 345198Adams' catalyst촉매HCID 8857Ethyl Acetate용매

실험 절차

39 mg of PtO2 (Adam's catalyst) was added to the mixture of 7-(8-azabicyclo[3.2.1]oct-2-en-3-yl)-5-(2chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one (77 mg) in 2 mL ethyl acetate. The resulting reaction mixture was evacuated and purged with argon. Then hydrogen was bubbled through and the reaction mixture was stirred under hydrogen for 8 h. The reaction mixture was filtered, concentrated under reduced pressure, and purified by preparative thin-layer chromatography, eluting with 95:5 CH2Cl2-2M NH3 in methanol to yield 7-(8-azabicyclo[3.2.1]oct-3-yl)-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one. Mass spectrum (ESI) 528.6 (M+1).

후처리

  1. customThe resulting reaction mixture
  2. customwas evacuated
  3. custompurged with argon
  4. customThen hydrogen was bubbled through and the reaction mixture
  5. filtrationThe reaction mixture was filtered
  6. concentrationconcentrated under reduced pressure
  7. custompurified by preparative thin-layer chromatography
  8. washeluting with 95:5 CH2Cl2-2M NH3 in methanol

출처 및 근거

ORD 기록
ord-7455c8041f97409eb6b326d97a931f03
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809199B2

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